- Audience-Alienating Premise: Adam Sandler playing twin brother and sister didn't exactly spell award winner. Add in immature Toilet Humour derivative of Sandler's films in general, Adam Sandler's growing poor reputation at the time and negative stereotypes towards Mexicans and mix them all together, and you get this movie.
- Bile Fascination: The fact that the film holds the record for most Razzies won and is considered one of the worst films ever made certainly helps.
- Critical Research Failure: The film claims that Jack and Jill are "identical" twin siblings, for the sake of having Adam Sandler's face on both a man and a woman. Identical twins are made from a single fertilized egg cell, which results in single-gender offspring. Fraternal twins are from separately fertilized egg cells and almost always subvert Strong Family Resemblance as a result, counting as twins because they were born at roughly the same time.
- Ensemble Dark Horse: Al Pacino, because he was the only character that anyone in the audience one could care about, compared to the unlikable cast.
- "Funny Aneurysm" Moment: Jill accused Subway spokesman Jared Fogle of hanging out with two hookers as a joke in the film... before Fogle was found guilty of possessing child pornography and having sex with minors.
- Funny Moments: Yes, even with a movie like this, there are a few genuinely funny moments here and there.
- A meta one for the Razzies for awarding Adam Sandler "Worst Actress" for his portrayal of Jill.
- Jack accidentally breaks Al Pacino's Oscar, and immediately apologizes, saying he's sure he has more. Pacino shrugs and says "Eh, you would think it, but oddly enough, I don't."
- Similarly done later, when Pacino mentions that he'd raised pigeons when he was younger... only to admit that he confused himself with Marlon Brando.
- Hilarious in Hindsight:
- After reviewing the commercial for Dunkin' Donuts, Pacino demands that Jack "burn this" and every copy of it after expressing disgust at the results. Many viewers and critics were quick to reinterpret this scene as a stab at the movie itself after they had seen it for themselves.
- Just Here for Godzilla: A good chunk of Mexican viewers went to see the movie because it was the first foray of comedian Eugenio Derbez into a Hollywood film. Most of them were disappointed since his role in the movie was far smaller than the advertisements in Mexico made them believe.
- Memetic Mutation: The CGI bird in the chocolate fountain gained quite a life of its own over on Tumblr.
- Money, Dear Boy:
- Cinematographer Dean Cundey, whose resume includes such beloved genre hits as Back to the Future, Jurassic Park, and the early films of John Carpenter, worked on this. The only thing more astonishing that than is the idea that the film actually had a cinematographer in the first place.
- RedLetterMedia looked into the film's production (complete with Conspiracy Wall) and argued that Sandler made the movie to exploit the complexity of the studio system, having used the web of overlapping parent companies to cram the movie with product placement and justify his exorbitant budget.
- The Scrappy: Jill, for being rude and annoying and complaining a lot.
- Signature Scene: "What's my name? Dunkaccino!"
- Special Effect Failure: Most of the effects shots used to show Jack and Jill interacting on-camera are admittedly quite impressive, but there are a couple of shots, particularly on the cruise ship, where Jill's head doesn't quite sit on her body correctly, creating an Uncanny Valley effect.
- Squick: The scene where Jill cuddles up with Jack with the former giving a Slasher Smile gives out incestuous undertones.
- Strawman Has a Point: As mentioned below, when Jack's wife scolds him for yelling at Jill. Jack is meant to be Made Out to Be a Jerkass; however, Jack has every right to alienate his sister for being rude to anyone she meets and being a public nuisance. Along with Jill invading her brother's privacy when it's made clear that she's overstayed her welcome.
- Took the Bad Film Seriously: Al Pacino's performance was the one part of this movie critics agreed was good, next to his Dunkin' Donuts commercial.
- Unintentionally Unsympathetic: It's clear that whenever Jack yells at Jill, we're supposed to be siding with Jill, but she's often very rude and nasty to everyone she meets, and is generally a public nuisance, like when she takes a call while watching a film and then complains about how the people trying to shut her up are being so loud she can't hear the phone. She also invades every aspect of Jack's life (and had been invading upon every aspect of his life for years), even though it's clear he doesn't want her there, even extending her stay over many more weeks without asking Jack.
- Wangst: Of all the things that Jill overreacts to, her freak-out at not having her own birthday cake at the party stands out, especially seeing how anything like the ginormous cake that her and Jack actually got would have to be ordered weeks (if not months) in advance, and Jill wasn't even originally supposed to be at the party.
YMMV / Jack and Jill